The Tragic Life of Charlie Trout
by poptartphreak
Summary: Chuck sat on the ledge because, one day, he would finally find the nerve to do what the world seemed to be tempting him to do since birth: jump.
1. Prologue

The Tragic Life of Charlie Trout Prologue

The average human body contains a little over five liters of blood. Bart could estimate no less than three liters of his wife's blood was coagulating on the formerly shiny blue tiles of the operating room floor. Another half liter was carelessly smeared across every available surface. Gloved hands, surgical gowns, and gleaming stainless steel instruments and trays were mottled with angry streaks of crimson. And there was a further half liter in the scarlet saturated gauze pads that littered the floor, squishing wetly under the feet of the surgeons working feverishly to save his wife. And though brilliant red bags hung from two IV poles, attempting to rapidly put back what had been lost, Bart knew his wife was dying. He could already feel the hollowness created by her absence and his eyes burned stubbornly with unshed tears.

This was not how this day was supposed to end.

Four Months Earlier…

Bartholomew Bass had never envisioned himself in the role of a father. But there he sat, with his large hands splayed carefully over his wife's enlarged belly, in silent awe of the soft flutters their son's movements created under his fingertips. Bart and Misty didn't have the typical Upper East Side marriage, deeply mired in lukewarm feelings of affection and secrets. Bart loved his wife dearly. He would have given her the stars if she'd only asked. But she didn't want a heavenly body, just a single body, one she could cradle in her arms and rock to sleep at night. She wanted a child. She wanted a little boy, full of playful mischief, who would bring a smile to Bart's normally sullen expression. Or a little girl, sweet and innocent, with dark brown ringlet curls and expressive eyes who would help to soften Bart's hard exterior. And because Bart could never say no to her, Misty quickly found herself temporarily providing room and board to the new heir of Bass Industries, Charles Bartholomew Bass.

"We'll call him Charlie," she had told Bart through flushed pink cheeks as soon as they'd settled on a name. "Charlie Bass," she announced as her hand settled on her swollen belly proudly, rubbing gentle circles. "We're going to have our hands full with you." She smiled, feeling the baby's restless activity as he reacted to the sound of her voice. "You are going to be nothing but trouble, just like your father. I can already tell," she teased before giving a contented sigh and snuggled into Bart's embrace.


	2. Chapter 1

Chapter One

_Click, clack._

_Click, clack._

_Click, clack._

Bart's quick footsteps echoed down the lonely and deserted hospital corridor. Technically, he wasn't allowed in this particular corridor. It was for hospital personnel only.

_Click, clack._

_Click, clack._

_Click, clack._

Technicalities never stopped Bart Bass, and neither did the bulky rent-a-cop who sat at its entrance. Anyone else and the overzealous guard would have gleefully taken the opportunity to test out his new hospital-issued taser. But one cold and withering look from Bart was enough to strangle any words or thoughts of action from the guard's underused brain. Instead the guard had just nodded dumbly, letting Bart breeze through unchecked.

_Click, clack._

_Click… clack._

_Click… clack._

His quick, businesslike pace slowed as he approached the operating room entrance and Bart could feel his breaths coming in shallow bursts. Even as he felt his pulse pounding in his ears, he left the comforting fluorescent glow of the corridor hallway for the dark shadows of the abandoned operating room. Bart stood motionless in the middle of the operating room. Though hours had passed and undoubtedly gallons of disinfectant had been scrubbed into the tiles, the room still held the faint metallic smell of blood. Bart closed his eyes and was flooded with the grotesque, blood-splattered images of his wife's last hour of life. He shook his head quickly, trying to push the images from his mind. Where had this day gone so irrevocably wrong?

Twelve hours earlier…

"Oh my," Misty had laughed until tears streamed down her face at the sight of her husband, standing uncomfortably in the entrance of the room in a rumpled set of hospital scrubs. This was why she loved this man. The exterior that he showed the word was made of steel. But his insides were made of something much, much softer. In all her years of marriage to Bart Bass, Misty knew there were three things that Bart hated: 1) the sight of blood, 2) the smell of hospitals, and 3) the absence of a perfectly pressed trouser crease. And for her, to ease her discomfort and nerves, he had faced all three at once.

For all the ridicule, Bart simply held his head a little higher and strode purposefully into the room. Even in wrinkled and worn scrubs, he was a formidable sight. The nurses quickly scurried to get out of his way as he breezed through the room, stopping only when he was at the side of his wife's hospital bed. Misty had reached her hand out to him then, grasping his hand tightly until his eyes lowered to hers. "Thank you," she had murmured quietly. A smile flickered briefly at the corners of his lips as he squeezed her hand in response. For some emotions, there are no words.

A high-pitched beep from a machine to Misty's left distracts Bart. The blood pressure cuff secured around his wife's thin arm inflated suddenly and she winced under the pressure. Bart strokes her free arm with his fingertips, trying to distract her. But once the cuff deflated, Bart's eyes move back to the red, digital numbers displayed. Instantly, his eyes narrow. "Her blood pressure is low," he barks in the direction of the nearest doctor. While Bass Industries has made a sizeable contribution to this hospital to ensure the best care available, Bart isn't taking any chances. There isn't anything worth more to him than the two people in front of him, not even Bass Industries.

"Uh," the doctor fumbles, momentarily surprised at Bart's astute comment. "90 over 50," he reads. "You're right. It's on the low side, Mr. Bass. But it isn't anything to worry over just yet. We just administered the epidural a few minutes ago. Sometimes we observe a temporary drop in blood pressure for some people. It's nothing serious, just something that needs to be monitored."

"Do you think I donated a new wing to this hospital for my wife to be treated like everyone else?" Bart growled, his voice dangerously low and threatening. "Do you have any idea who you are dealing with?" He asked but didn't wait for an answer. "Let me explain this in terms you'll understand. This is Mrs. Bass. She is not now, nor will she ever be, classified as "some people". I suggest that if you don't want to find yourself suddenly unemployed, you will keep a much closer eye on my wife. We're not playing the wait-and-see game. If something goes wrong—"

"Bart," Misty warned quietly, shaking her head as soon as his eyes connected with hers. She reached out for his hand instead, letting the warmth of his large hand seep into her chilled skin.

And that was all it took to reign in the great Bart Bass. He glared menacingly at the young doctor before returning his attention back to his wife. "I'm just making sure you're taken care of," he told her quietly, glancing up again to make sure the doctor was heeding his words.

"They're taking wonderful care of us, Bart," she assured him with a gentle smile, squeezing his hand once more to regain his full attention. "Everything is going to be fine."

If only that had been the case.


	3. Chapter 2

It was hard to understand how both the happiest and saddest moments of Bart's life coexisted on the very same day. It was even more puzzling to know that they had both occurred within an hour of each other. One life had barely begun just as the other was prematurely ended.

The steady sound of Bart's shoes against the cold tiles of the hospital corridor faltered as he winced suddenly at that thought. How terribly cliché. But that's all this entire situation was. He wasn't sure when it happened, but, sure enough, his entire life as he knew it had suddenly become one big, horrible, tragic cliché. A young and beautiful wife: dead before her 30th birthday. Killed during childbirth, killed by a child she wanted more than anything else in the world. And now he played the part of the broken-hearted husband and newly minted single father, left alone in the middle of it all. He was numb, defeated, and confused. The emotions were conflicting, diametrically opposed like trying to shove the like poles of a magnet together. They were incompatible, one always forcing the other away. Should he laugh, delight in the birth of his only son? Or should he cry, grieve for the soul wrenching loss of his wife?

Whatever the correct answer was, if there was a correct answer, Bart did neither. Instead he lashed out angrily at anyone or anything within his eyesight or reach. He felt shafted, lost, and completely unprepared. Suddenly Bart Bass found himself thrown headfirst into a situation where he couldn't buy a more favorable outcome. No flash of cash would bring her back. No matter how many zeros appeared behind the one on a donation check, her body would still be draped, pale and lifeless, under a plain blue sheet in the hospital morgue. Nothing could right the world of the wrong that had occurred today. Nothing could bring her back. And so he knocked over silver trays of blood caked instruments to the equally blood stained floor to share his anguish. He yelled, threatened, and cursed, but to no avail. It changed nothing. His world was every bit as lopsided and wrong as it had been before his temper tantrum. Throughout all of this, not a single tear fell. Even crying didn't seem like an adequate enough response for losing the other half of his soul. It scared him to think that at that moment, he wasn't sure anything, or anyone, was worthy of that loss. He spat the boy's name out as a curse as he stalked from the operating room, leaving the contents of the room just as chaotic and torn apart as his heart.

He and Misty had spent months preparing for this day, each in their own way. She had spent months and undoubtedly hundreds of thousands of dollars creating the perfect nursery for their son. She had hand selected only the finest, refusing to accept anything but the best for their future progeny. And Bart had indulged her every whim, wanting nothing more than to see her happiness evident in her smile. But while she had fussed over nursery room murals and plush teddy bears, Bart had taken a more theoretical approach. He had devoured every book he could find on pregnancy and parenting, desperately attempting to make up for the parental instincts he knew that he lacked. Warmth and open affection had never been his strong points, but strategies and schemes were like second nature to Bart Bass. By the end, he understood the basic physiology behind pregnancy and child birth; he had educated himself about ever major complication that could occur, paying special attention to any tell-tale symptoms; and he studied a multitude of approaches to parenting, masterfully weaving bits and pieces of the various methods together with the string of his own hardnosed personality. It was never his intention to be his son's best friend. Bart's own father had given him that. Friendly smiles, long talks, and warm hugs. Worthless, all completely worthless, when you rot in poverty and go to bed hungry. Bart would give his son structure, wealth, and, eventually, the keys to the empire he had built from scratch.

After a decade of carefully made plans going exactly as scripted, it was a shock to Bart when everything fell apart. No matter how many times he went over it in his head, he could never pinpoint the exact moment where the situation shifted from being a difficult birth to a life threatening birth and imminent death. And despite his most arduous efforts, Barth couldn't even find a single mistake or misstep made by the medical team. Even after he violated every HIPPA regulation in the books by snatching his wife's medical chart from the front desk and spent hours combing the scribbled words, he found nothing. All Bart could see was the perspiration staining the resident's scrubs as he strained with CPR long after Misty would have been brain dead, the anxiety in the his voice as he barked orders and frantically tried to stop the bleeding, and the tears shimmering in the young resident's eyes when he'd finally announced the time of death. It was, as it was so often put, a fluke. It was nothing that could have been either predicted or prevented. There was no one to blame, so Bart blamed himself.

A deep sigh escaped from between Bart's lips as he continued to amble down the empty hospital corridors. It wasn't until he heard the piercing shriek of an infant that he realized he was standing in front of the nursery. This impromptu trip hadn't been intentional. In fact, he'd purposefully stayed away until now, unsure if he could balance out the conflicting floor of emotions that just the thought of the boy brought to his mind. But curiosity won, as Bart had barely had a glimpse of the boy after the birth. And even that had been a fuzzy blur in his memories for the day. He could remember the soft slap of gloved hand against plump backside followed by the angry and loud wail of their son. At the time, their son's cry was a sound that had very nearly stopped his heart, suddenly turning the past nine months of being little more than a bystander into something much more tangible and real. And then everything had gone wrong at once. The relief that Bart had felt, knowing their son was alive and well, was quickly replaced with panic. Suddenly there was blood everywhere and no way to stop it. During the chaos, Bart had only barely registered the general murmurs of good health coming from the nurses cleaning up his son. He'd been too focused on Misty to take in the particulars, clinging tightly to her hand in desperation. In the end, it hadn't mattered. Her life had still slipped from between his fingertips.

Bart set his jaw and willed himself to look into the nursery. He may have lost his wife, but he still had the little boy she had died to give him. And that little boy was the only tangible part of her that had survived the tragic afternoon. He scanned quickly over the occupied cribs and quickly found himself sucking in a loud breath at the sight of the small and placid infant swaddled in a soft blue blanket. Charles Bartholomew Bass, the name plate read. His son. And Bart could see the resemblance immediately. But it was not his own features he saw reflected in the boy. He saw Misty's nose and mouth rearranged on the baby's face. He could see her dark hair in the soft, downy fuss that covered the boy's head. And Bart was sure that the boy's bright blue eyes would eventually darken to the deepest of browns, just like his mother's eyes. Without thinking, a smile graced Bart's lips for a moment as he thought of how much this would please Misty. She had promised him a little dark hair, dark eyed boy, and she had been right. But the smile was quickly wiped away as Bart remembered that she would never get to meet the son that they had both eagerly anticipated.

And it was in that moment that Bart realized just how alone he truly was.


	4. Chapter 3

Chapter Three

Money can buy nearly anything. It can get you a reserved table at a fully booked restaurant, tickets to a sold out concert, or, in the case of Bart Bass, it can buy your son an extended stay in the hospital nursery despite having no medical abnormality. His grief was still too raw. The dirt was still fresh on his wife's grave, and Bart wasn't ready to plunge head first into the life of a single father. And it really was for the boy's own good. The only thing Bart knew about babies was that he knew absolutely nothing about babies. He had no clue how to prepare a baby bottle. Diapers were still a very sticky and confusing mystery. Bart had been so completely and utterly clueless that he didn't even know how to hold his own son. For fear of hurting the boy, Bart had spent the first few days of Charles's life just starting at the baby from behind the protective Plexiglas of the nursery window until a kind nurse took pity on him.

"What a handsome little boy," the nurse had cooed. "What's his name?" She asked pleasantly as she stood beside Bart at the nursery window.

Bart had nodded his head in response. "Charles," he answered quietly. "It was his mother's idea."

"Charles," the nurse repeated his words. "What a lovely name."

They stood together in silence, just watching the boy's jerky movements. "Wouldn't you like to hold him?" She asked finally, turning to him once more.

"I, uh—" Bart sighed, looking around to make sure no one else would hear. "I-I don't know how," he mumbled quietly, the words almost running together. He cleared his throat, straightening his tie.

"Come, come," she insisted, smiling at him and beckoning him to follow her into the nursery. "If that's the only thing that's stopping you, we can fix that very quickly."

"Oh… I don't know…" Bart faltered. There was nothing he hated more than feeling incompetent.

"Nonsense," she dismissed his protests with a wave of her hand. "This is your son. You'll have to hold him eventually. The help can't do everything for you," the nurse teased with a smile. "There's nothing to it. I promise." She said, stepping forward and using her slender hands to expertly lift the boy from the crib before cradling him against her chest. "The key is to be sure to support the head," she explained before depositing the baby back into the crib. "Now you try," she said, moving back so Bart could move closer to the crib.

Despite her instructions and demonstration, Bart was still skeptical. But upon the nurse's continued encouragement, he tentatively reached his hands into the crib. His long fingers curled underneath the little boy's armpits. Bart barely had the baby an inch above the crib mattress when a loud squeal erupted from Charles's lips. Ironically worried that he'd somehow hurt the boy, Bart had quickly jerked his hands away and unceremoniously dropped the boy back to the crib mattress.

Despite the nurse's reassuring words that no long-term harm had been done, Bart didn't touch his son again for a week.

And Bart was convinced that he had inflicted permanent brain damage on his son. He spent the entire afternoon combing through the piles of job applications for a nanny.


	5. Chapter 4

Chapter Four

The first few years were the hardest. There were many times during those first few years following Misty's death when Bart honestly felt that the empty ache inside his chest would kill him, that the all consuming grief of his loss would eat him alive. And for the first time in his life, Bart seriously considered suicide. At first it was just a stray though here or there. And then he would catch himself, suddenly startled at the vivid imagery taking place behind his eyes as he focused too intently on the shiny, sharp knife sitting in the kitchen sink, the thick, sturdy rope that was in his desk drawer, or the bottles of prescription pills lining his medicine cabinet. It was tempting, the idea of putting a quick end to the mess his life had become. A few painful moments seemed worth permanently erasing the enormous weight of grief and loneliness that was slowly crushing him. It was during his darkest hours that Bart was thankful for the Catholic guilt his father had spent years instilling in him. Though he was far from a religious man, it made banishing the thoughts from his head much easier when his world was defined only in terms of black and white.

But even his Catholic guilt couldn't suppress his mind's need to see her again. Bart's eyes and heart betrayed him on a daily basis. He saw her everywhere: walking on the street, in a crowded restaurant, at the opera. His eyes saw her in every woman with dark hair and a fair complexion that he passed. He would stop and stare, breathless and transfixed, until his eyes would refocus and she would disappear. Even Bart's sleep was haunted by her images. Sometimes he would wake up in the middle of the night, alone in the bed they had shared, with her scent tickling his nose. His heart would thump wildly in his chest, his treacherous mind working overtime to convince himself that the past year had been nothing more than a very realistic bad dream. And just when his strong sense of logic would begin to buckle, to buy into the happy ending he wanted to desperately to believe, Bart would sprawl his arm across the bed in search for her warm form. But, every time, his hand encountered nothing but the cold sheets beside him, still empty and untouched. It was like losing her all over again.

The baby added another layer of complication to Bart's already complicated life. It wasn't that the boy caused Bart much trouble directly. He had hired more than enough people to ensure that his son was well fed, groomed, and content. Safe, experienced hands held, changed, and dressed the baby while Bart kept his distance. When Bart's work hours stretched longer and longer, he had convinced himself that nothing was wrong. He wasn't intentionally avoiding going home, and he certainly wasn't avoiding his son. Bass Industries was growing more rapidly than ever before, he would tell himself. If he didn't keep up now, then all the years of hard work it had taken to reach this point would be lost. Bart was busy making sure that his son would inherit a dynasty rather than a disaster. And really, he wasn't missing much. Bart saw nothing wrong with the videotaped milestones sitting in his bedroom. Charles's first smile, his first steps, and his first coherent words were all captured on video. They were all neatly labeled, organized, and collecting dust as they sat unwatched. He would work hard now, Bart would reason with himself. Then he would be able to relax and spend time with the boy once Charles could spit out a string of vowels and consonances in logical patterns.

But an absentee parent did nothing to halt Charles's rapid growth. And with every passing day, the boy's resemblance to Misty grew. If, by some miracle Bart had made it through the day without being plagued by illusions of his wife, he would come home and one glance at his son's face would bring it all back in a rush of overwhelming emotion. What used to be a part of his morning routine, holding the little boy in his arms with a morning bottle as CNN covered the morning's headlines, became more and more infrequent. And Bart hated himself for it. The baby—his child—deserved so much better.

It was close to Charles's second birthday when Bart realized what needed to be done. "We're moving," he declared suddenly as he watched as his son toddled on unsteady feet in front of him.

"Moving, sir?" The young nanny questioned as she mirrored Charles's progress across the room, her gaze never leaving the little boy, ready to catch him if he should fall.

"Yes," Bart answered simply. "Several months ago Bass Industries purchased a luxury hotel, The Palace," he explained. "It's across the street from the office. I've had them prepare a penthouse suite for us. I'll be selling the house immediately." Bart paused for a moment, his jaw clenching momentarily in concentration before he continued. "This place," he said softly. "This place reminds me too much of his mother. It holds too many memories. I—We need to get away from here. I can't keep hiding here… in her memories. It's time I moved on. She wouldn't have wanted me to do otherwise. And Charles deserves a home of his own, not a shrine to a deceased parent he never knew." Bart responded thoughtfully, more to himself than anyone else.

His head snapped back to the nanny. "I want all of Misty's things packed up and placed in storage. Clothes, shoes, photos," he listed off the items. "Everything. I want it packed away. Today." Bart said, his lips curling into a faint smile as he watched his small son latched on to his pant leg and tilted his head back so he could clearly see Bart's amused face. "Da," the little boy declared triumphantly.

In an uncharacteristic display of warmth, Bart Bass bent down and scooped his son up into his arms. "That's right," he told the little boy as Charles rested his cheek against Bart's shoulder. "I'm your Da."


	6. Chapter 5

Chapter Five

Charles Bass sat on the floor of his father's study, a detailed wooden city that mirrored the Manhattan skyline sprawled out in front of him. The little boy ran a shiny red car along the painted black roads that crisscrossed the towering buildings, his lips puckered in silent car engine noises. As he maneuvered the car around a hairpin curve, the silence of the room was suddenly broken by the booming sound of his father's very angry voice. Charles flinched and his head snapped upward by reflex, his eyes wide, momentarily terrified he had done something to upset his father. And then he realized Bart hadn't even turned in his chair. Craning his neck, Charles's pounding heart began to slow as he realized that Bart was yelling into his cell phone rather than at him. This was confusing because, up until now, that voice had been reserved specifically for him when he had done something particularly bad. Like the time he had tried to see if Bart's laptop would float in a bathtub full of water, or when he had shredded a stack of papers that Bart had brought home from work to make confetti.

With the toy car clutched in one hand, Charles left the toy city behind and walked across the room to the couch. He leveraged his short legs onto the couch, crawling on his knees across the slick leather upholstery as he scooted himself closer to his father. Bart was seated just behind the couch at his desk, still arguing into his phone, albeit at a much lower volume now. Charles draped his free arm over the back of the couch, letting his chin settle into the crook of his elbow as his dark eyes studied the movements of his father. At the age of four, relationships were supposed to be simple. He was supposed to have a family that consisted of a mother, a father, and maybe even a little brother or sister. They were supposed to live in a small house with a fenced in back yard and a dog. That's what all the storybooks said. All the storybooks lied. That was life lesson number one for young Charles.

He and Bart lived alone in the penthouse suite of the Palace, where the closest thing he got to a backyard were the fake plants in the hotel lobby. He had no mother. The women Bart brought back up to the suite when he thought Charles was asleep didn't count because he rarely saw the same face two nights in a row and they were always gone in the morning. Charles wasn't completely sure, but he thought that a mother would probably stick around for a little longer. She might even make him blueberry waffles for breakfast. Yes, he was sure that once he was the good little boy that Bart always sternly warned him to be whenever they were out in public, she would come home.

It wasn't that Charles was deliberately bad. At least that wasn't always the case. He was just "playful". That's the word Bart used to describe Charles to the newest Nanny he managed to recruit into looking after him. One month of "playful" was all any Nanny had been able to take since he'd turned three and discovered his penchant for causing mischief. Honestly, it wasn't his fault that the same annoying, yippy dog that had once bitten him when he was two also happened to fit perfectly inside one of the large, decorative vases in the hotel lobby. And how was he to know that public urination was frowned upon? He'd just been trying to water the little palm trees that grew in potted plants near the front desk. They'd looked thirsty. But, if he was really honest with himself, Charles knew he caused trouble just to get a reaction out of Bart. After all, it's hard to ignore an unruly child when said child is under the close scrutiny of the public eye. And at four and a half, attention was attention, whether it was good or bad attention didn't really matter to him. For a few brief minutes (or hours, depending on how mad Bart was), Charles had his father's full attention.

"What are you doing, Charles?" Bart's deep voice boomed, the sudden noise causing Charles to jump. Buried in the depths of his thoughts, Charles hadn't noticed Bart end his phone call and turn around in his chair.

"Nothin'," the little boy answered quickly before amending himself. "Nothing, sir." Always proper English, always polite. Those were only two of the many rules Bart enforced that he constantly swore Charles would thank him for later in life.

Bart's frown remained etched into his features even after the boy corrected himself. "Go tell the Nanny to get you cleaned up and changed." He glanced at his watch. "We've got to meet with your new teacher tonight. It's open house."

"But I don't wanna go to school," Charles whined in the truly obnoxious way that only a four year old can. "I could go to the office with you," he bargained. "I'd be good. I promise."

Bart gave a wry smile "Like how you were good this morning when you pinched the line of Mr. Eastwood's oxygen mask?"

"He's mean!" Charles defended himself against the evil old man that lived below them.

Sighing, Bart shook his head. "This isn't a discussion. You're going to school. It's where you belong." When the boy didn't look the slightest bit convinced, Bart continued. "Besides, all of your friends will be there. Uh, Blair Waldorf, Serena van der Woodsen," he named off the children of the families he knew.

"Girls," Charles muttered darkly, his mouth twisted in distaste.

"There will be boys, too," Bart amended. "Uh, the Archibald boy," he floundered, unable to remember the child's name. "The Captain's boy."

"Nathaniel," Charles supplied, looking a little more convinced.

"Nathaniel," Bart repeated. "He'll be there too. Now go," Bart shooed Charles away with a wave of his hands. "Get dressed."

Bart sighed when Charles made no movement to do as told. "Now, Charles. Get moving!"

In a flash, the little boy stood from his crouched position and jumped off the couch, running at full speed out of the room and down the hallway.

Bart winced, calling after the boy. "Shoes off the couch, Charles! And stop running in the house!" He sighed again as he shook his head, knowing at his orders had gone unacknowledged by the gradually fading sounds of Charles's shoes slapping against the floor as he ran. "Misty," he murmured. "What did you get me into?"

***

"Where did you get that?" Bart asked, eyeing his son's new vivid purple bowtie. After sliding himself out of the limo, he turned around and attempted to help the little boy in exiting the limo.

Charles dodged Bart's outstretched hand, jumping from the limo just to hear his dress shoes slap hard against the pavement "I bought it," Charles announced proudly, almost losing his balance.

"But purple?" Bart questioned as his hand shot out, catching the back of Charles's suit jacket just before he would have face planted onto the pavement. Bart was just starting to get used to the fact that his four year old son preferred to dress like a 40 year old man… if that 40 year old many had been born in the 1930s. But purple bowties? That's where Bart drew the line.

"I like purple," Charles declared, weaseling out of Bart's grasp.

Bart sighed. The boy liked purple and hated girls. So his son was gay. There were worse things in life. Maybe he should send him to Catholic school later. The Catholics could beat the gay out of him with threats of hellfire and brimstone. "But isn't purple more of a girl's color?"

Charles thought about this for a moment, his childish features scrunching together in thought. "But girls don't wear bowties," he reasoned.

Bart stopped in his tracks, blinking at the little boy who stood beside him. Had he really just been out smarted by a four year old? With another sigh, Bart shook his head and dropped the argument. "Hold my hand," he ordered dryly, reaching for the little boy's hand now that they had reached the front door of the school. There were too many other children around and Bart knew Charles's penchant for wandering and causing trouble. Maybe they could get through introductions before the teacher realized his son was a holy terror. But Bart's hand jerked away from Charles's when they'd barely made contact. "Christ, Charles. What have you got all over your hands?" He asked, his lips curling in disgust. "How did your hands get all sticky?" Bart demanded as he pulled his handkerchief from his pocket and wiped his own hand before moving to the boy's hands.

"The doorman gave me some candy," Charles answered reluctantly, knowing this would displease his father. And sure enough, another disapproving frown creased Bart's features. Some days Charles wasn't sure he could ever make his father happy.

"I'll have to have a talk with him," Bart muttered, mostly to himself as he wiped the sticky remnants of candy away from Charles's hand as best he could. "Com'on," he said, grasping the boy's hand once more. "Let's find your teacher."

They had barely made it past the front door before they were accosted by young woman. "Hello," she greeted them, bubbling with energy as she reached forward to shake Bart's unoccupied hand. "I'm Miss Hannah," she beamed.

"Bart Bass," Bart stated simply, his expression still grim, not bothering to return the woman's smile.

"Very nice to meet you, Mr. Bass," Miss Hannah said as she checked her class roster. When she'd found the appropriate name, she glanced up, smiling warmly at the little boy that stood, almost shyly, beside Bart. "And you must be Charles Bass."

"Yeah," Charles answered abruptly.

"Excuse me?" Bart snapped, his stern glance transferred to his young son and his lack of manners.

"Yes ma'am," Charles corrected himself quickly, casting a quick and worried glance at his father.

Miss Hannah, ignoring the slip in manners, stooped slightly so that she was eye level with the boy. "You'll be in my classroom this year. We're going to have a great time together, Charles." She paused for a moment, consulting her class roster to see whether the little boy had a preferred nickname. Charles was such a formal name, much too serious for the mischievous little boy standing in his father's shadow. When she saw that nothing had been listed, she gave a momentary frown before continuing. "What name do you prefer to be called?" She asked the little boy.

"My name is Charles," the little boy responded immediately, not understanding her meaning.

"Oh, I know that," Miss Hannah laughed at the sudden seriousness in the boy's tone and expression. "I just meant to ask you whether you prefer to be called Charles, or do you go by a nickname? Charlie? Chuck?" She patiently explained.

It was obvious this had never occurred to the boy. His eyebrows knit close together in concentration as he considered his teacher's words.

"His name is Charles," Bart cut into the conversation, hoping the bite to his tone would be sufficient of an explanation.

So deep in his own thoughts, Charles hadn't even registered his father's words. "Charlie," Charles Bass decided with a grin, still paying little attention to his father. "I want to be called Charlie. Like in the book with the candy factory," he explained eagerly, mentioning one of his favorite books that his Nanny had read to him over the summer.

"No," Bart growled out in a tone that caused both Miss Hannah and Charles to flinch. The grin that had been lighting up the little boy's features was wiped from his face in an instant. "You will not be called Charlie. Don't let me ever hear you say that name again." Bart fumed as sudden images of Misty he'd fought hard to suppress were resurfacing at the sound of the name she'd wanted to call their son. "His given name is perfectly fine," he hissed venomously.

The young boy swallowed visibly and glanced back to his father once more before addressing Miss Hannah. "My name is Charles," he answered quietly as his dark eyes now focused on the ground.

"Uh, well," the teacher spoke again with false enthusiasm, attempting to move on to a less controversial subject. "How about I tell you about what we'll be doing this year? We'll start first with our—"

"My name is Charles Bass," the little boy interrupted her, speaking the words louder now that he had stepped to the side of his father's impressive shadow. There was a defiant set to his jaw and a mischievous glint in his dark brown eyes. "But you can call me Chuck." The little boy paused for a moment, smirking. "I'm Chuck Bass."


	7. Chapter 6

**Author's Note: **This took forever to write, and I'm still not completely satisfied with it. But I'm also tired of revising and editing, so I'm throwing it out there anyway. Thanks to everyone who has taken the time to leave feedback. It's greatly appreciated! Thanks for reading.

Chapter Six

Once upon a time, Bartholomew Bass dreamed of being a good father. Even after Misty's death, he tried to approach the idea of being a single father as something new to conquer. And the great Bart Bass never backed down from a challenge. Still, he was almost startled by the silly and illogical thoughts that floated through his head on occasion, entertaining the idea of stereotypical traditions such as happy family dinners, a son who brought home glowing report cards, praise-filled parent-teacher conferences, and two box seats at the Rangers games. In his fanciful daydreams, his son would be a miniature version of all Bart's good traits. Along with his mother's good looks, he would be an ambitious, serious, hard working little boy who missed absolutely nothing and had an instinctual feel for finances. He could easily imagine the little boy growing up, transforming into a socially eloquent young man with whom Bart could share trade secrets with over good scotch and some Cuban cigars. The boy would be his son, his protégé, and his friend.

But that's the problem with indulging in idealism too often. The lines between fiction and reality start to blur. You forget that the cold truth is that you can't get more out of a relationship than you're willing to put into that relationship. It's a mathematical impossibility. Even the great Bart Bass can't violate the laws of thermodynamics and create something out of nothing. Because leaving for the office before dawn and arriving home well after sunset made for very rare and awkward family dinners, few heart-to-heart chats, and, outside of signing a fat donation check to the school, a complete absence of involvement in Chuck's schooling. And so Bart was just beginning to reap exactly what he had sowed for the first twelve years of Chuck's life, a son who shared little more than a roof, a Y chromosome, and the same last name with Bart.

It wasn't that Bart didn't care about his son. Despite what others thought, Bart cared deeply for the boy. He simply lacked the ability to step out from behind his stoic façade. And so instead of hugs, he gave the boy anything he needed, wanted, or looked at for more than three seconds. As if overindulging his son with physical possessions would somehow compensate for a complete lack of emotional support. And so the uptight little boy who enjoyed making a mockery of conservative formal wear grew up to be as emotionally cold as his father. Bart watched as the serious little boy with an innocent mischievous streak developed into something that was potentially much more sinister as he approached his teenage years. But most of all, Bart saw all the wasted potential. Highly intelligent, highly persuasive, but the boy was too lazy to use either trait for something that didn't directly benefit him. So much wasted potential.

Bart tried hard not to let his disappointment show, because he was all too well aware of his own shortcomings. As kind and loving fathers go, Bart was a complete failure. And so he retreated into his work, focusing on what he could control and what he excelled at at while continuing to hope that the relationship he had with his son would one day fall into perfect alignment, preferably without any messy emotional scenes. But it wasn't in Bart's nature to admit defeat. Despite their strained father-son relationship, Bart knew exactly what went on in the boy's life. They had no secrets. No surprises, that was Bart's well versed motto. And that's exactly how Andrew Tyler came to be a full-time employee of Bart Bass.

"_And can you give me a physical description of him?" Andrew Tyler asked, his pen poised just above his legal pad. "A recent picture would be helpful."_

"_Of course," Bart nodded his head as he turned in his seat to pull a file cabinet drawer open. "Brown hair, brown eyes, generally in formal attire," he ticked off the description as he rifled through the files for a recent picture of Chuck. He paused for a moment, glancing at Andrew momentarily. "He likes bow ties," he said. "Bright ones," he added, his distaste clear in his expression. "Purple, pink, red, obnoxious plaid patterns," Bart continued as he returned to the files in front of him. _

"_Good, good, that will definitely help," Andrew commented as he wrote. "Height? Weight?" Andrew asked without looking up from his paper. When Bart didn't answer right away, Andrew glanced up. "It doesn't have to be exact, Mr. Bass. Just ballpark it." _

"_Uh," Bart hesitated, "maybe three foot eight and forty-five pounds."_

_Andrew's head snapped up immediately. "What?" He asked, sure he'd not heard Bart correctly._

"_I can get the exact measurements from the pediatrician," Bart continued, ignoring Andrew's initial reaction._

"_Pediatrician?" Andrew questioned again, his eyes narrowing with suspicion. "Are you joking?" He asked, already knowing the answer to that question. If there was one thing Bart Bass couldn't buy, it was a healthy sense of humor. "You want me to tail a kindergartener?"_

"_Of course not," Bart dismissed Andrew's comment, his tone annoyed as he continued his search through the many files in front of him. "He's in the first grade," he informed Andrew in a matter-of-fact tone, as if the difference between the two grades was monumental. "Ah, here it is," Bart said, removing a picture and passing it towards Andrew. "This is the most recent picture I have of him. It was taken last month, in the Hamptons."_

_Andrew lifted to picture to his eye sight hesitantly, still trying to figure out whether this entire meeting had been a gigantic practical joke. "You're not joking." It was a statement. There was no questioning tone. "You honestly want me to spy on a kid?" His eyes scanned the picture, his brow furrowing. Andrew had been warned about Bart Bass. Ruthless, cunning, and highly intelligent. Everyone had told Andrew that there was nothing the man wouldn't do to close a business deal. Nothing was too immoral, taboo, or illegal. Andrew felt a slowly creeping nausea clench his stomach and he began to regret accepting Bart's invitation for a consultation meeting. "Mr. Bass," Andrew shook his head, handing the picture back to Bart. "I can't be involved in this. I don't know where this is going. And I honestly do not want to know. But he's just a little boy. I have certain standards that I'm not willing to break. There isn't enough money for me to help you harm a child, even in the name of business. It's just not right." He said, gathering his things in a hurry, trying to rush out of the office before he felt the notorious wrath of the great Bartholomew Bass. "Let's just forget that we ever had this conversation. Anything else, Mr. Bass, and I would have—" _

"_Oh, for Christ's sake, Andrew," Bart Bass shot out in irritation. "This isn't business. He's my son."_

_Andrew froze, halfway to the door already with papers peaking messily from his briefcase. "Oh," he said simply, turning around. He studied the discarded picture that still laid face up on Bart's desk. Dark hair, dark eyes, a playful smile, and not a hint of resemblance to the man that sat in front of him. "Your son?" He questioned stupidly, still trying to make sense of everything._

"_Yes, Andrew," Bart stated drolly. "My son. Charles Bartholomew Bass. He turned six last month, attends the Browning school." When Bart noticed Andrew's skeptical gaze still inspecting the photograph, he answered the man's unasked question. "He doesn't look a thing like me. He has his mother's good genetics to thank for that."_

"_Mr. Bass," Andrew stated, finally removing his eyes from the picture of the boy. "With all due respect, I didn't become a private investigator to spy on kiddies at naptime. Take a look in the Yellow Pages. I'm sure you can find someone else who needs the money badly enough to do this for you. Spying on finger painting and recess don't require that much talent."_

"_I know your reputation, Mr. Tyler." Bart dismissed Andrew's protests with a slight wave of his hand as he pulled his checkbook from his jacket pocket and began writing. "I know that you're the best. That's why I contacted you instead of someone else. And since keeping an eye on a six year old boy won't be taxing, it'll give you plenty of time to complete some other… tasks… that I have in mind. You'll be compensated, of course." He finished, signing the check with a flourish before ripping it from the checkbook._

_Andrew blinked stupidly at the number of zeroes on his check, his mind trying to register the payment._

"_That's a monthly wage," Bart informed him. "For full-time service. I assume it's acceptable."_

_Andrew nodded his head numbly. "It'll do," he said meekly. "Uh, start on Monday?"_

"_You can start today. I'll expect weekly reports on Charles. The other… we'll discuss very soon." Bart said as he reached for the photography of Chuck to slide back into the appropriate folder._

"What do you have for me?" Bart Bass asked as he reclined in his office chair, propping his well-polished shoes on the edge of his desk in a rare moment of rest.

"It's uh…" Andrew Tyler trailed off as he tried to find the best way to phrase his response. Even after working for Bart Bass for over five years, he was still wary of the man. "It was an interesting week," he said finally as he sat down and pulled his blackberry from his briefcase.

Bart sighed, closing his eyes and pinching the bridge of his nose. "Tell me what happened," he said warily, already knowing he wouldn't like what he was going to hear.

"Your brother is creating a mess down in Australia. Luckily most of it's personal and you've got some really good people down there covering up Jack's messes. Everything has been under the radar thus far, but the man is pushing it. I was able to pay off the reporter who had pictures of him with that underage girl, but we might not be so lucky next time. Not everyone can be bought," Andrew said, glancing to the screen of his blackberry for his notes as he spoke.

"Next," Bart demanded without opening his eyes. He was well aware of his brother's lack of discretion. It was a sore subject.

"Harold Waldorf," Andrew let the name drop heavily in the room.

Bart opened his eyes cautiously, not liking Andrew's tone. "What about him?" He asked suspiciously. "Is he having second thoughts about buying into those lofts downtown? I thought I had him sold."

"Not exactly," Andrew said, frowning. "As far as I'm aware, there's little to no hesitation about the business deal. This is… personal, something I think you may want to consider before jumping into bed with him on this deal."

"Well?" Bart questioned impatiently. "Are you going to tell me, or should I just start guessing?"

After years of working for Bart, Andrew had become mostly immune to the man's insults and impatience. "You should probably know that Harold's been taking part in some extracurricular activities. If the past week is anything to judge by, these aren't just one time acts of indiscretion. It's becoming a habit."

Bart laughed bitterly. "That's not news," he scoffed. "This is the Upper East Side, Mr. Tyler. The anomaly around here is the couple where at least one individual ISN'T involved in some regular extracurricular activities. These people have no loyalty. It's what happens when money marries money."

"That's true," Andrew agreed. "But it is most definitely news when those extracurricular activities are of the same sex."

Bart rubbed his chin thoughtfully, giving a slight nod of his head. "Harold's gay?" He asked. "But what about Eleanor?"

"She doesn't know," Andrew answered. "And neither does their daughter. No one knows, really. He's only in the beginning stages of admitting it to himself. It happened for the first time a few months ago. I'm sure he had himself convinced it was a one-time thing brought on by too much wine and Eleanor being out of town. But then it happened again. And again." Andrew shrugged. "It's all legal enough, though the first one was on the young and scandalous side. It's Harold, so you know he'll be discrete. But it could come out, no pun intended. And considering the very conservative politics of your neighborhood, your profit margin could take a serious hit. It's not too late to pull out."

"No," Bart said firmly. "Harold's a good friend. The deal stays in place, regardless of his sexual preferences. Besides," he reasoned. "Lofts are marketed to a younger demographic who have much fewer hang-ups about sexual orientation. The deal stays. What else do you have?"

"Nothing major," Andrew continued as he scrolled through his notes on his blackberry, still trying to find the right way to bring up the topic he'd been dreading. "Lily van der Woodsen is single again. Dumped the German and moved back to the Upper East Side with the kids. The Baizen kid got busted for drugs. It was just a little pot, and it was nothing his daddy couldn't keep off the records with a little hush money. Chuck lost his virginity. Uh, the Vanderbilts will be in town next week. There'll be staying—"

"Pardon me?" Bart interrupted Andrew, a horrified expression crossing his features. "What was that?"

"The Vanderbilt's?" Andrew played stupid, trying to avoid talking about Chuck. "Anne Archibald's clan. They're going to—"

"Chuck did what?" Bart stammered.

"Lost his virginity," Andrew supplied. In all the years that he'd worked for Bart, this was the first time he'd heard the older man stutter, stammer, or lose his dignified composure. It was obvious that the news had surprised him, something that was difficult to do to Bart Bass.

Bart was silent for a moment. "H-how is that even possible?" Bart demanded to know. "You must be mistaken. He's nine years old, for Christ's sake! It's physically impossible."

"Twelve, actually," Andrew said with a grimace. This was not going well.

"Twelve," Bart repeated, frowning. "Really?" He asked in confusion.

Andrew simply nodded his head.

"And twelve year olds can have sex?" Bart asked, the same horrified expression still etched into his features.

Andrew shrugged his shoulders. "It would seem so."

"Oh god," Bart groaned, rubbing his hands roughly across his face, scratching against the beginnings of a five o'clock shadow. He was silent for a long, awkward minute before he moaned out the question that was nagging him. "Boy or girl?"

"Girl," Andrew answered swiftly. "Georgina Sparks," he said, supplying the answer to Bart's unspoken next question.

"You're kidding," Bart scoffed in disbelief as he studied Andrew's features for even a hint of jest. When he saw none, he swore loudly. "Jesus Christ. Leave it to Chuck to fuck the one girl who is perhaps a bigger liability than himself!"

"Blame it on the Champaign," Andrew said. "It was a one-time thing. They were at a party. He left her about an hour after she fell asleep. He's been pretty successful in avoiding her since, not that I blame him. The girl is unstable. There's uh… there's one more thing."

Bart looked up expectantly but said nothing.

"You might want to talk to Chuck about using protection. It seems as if he and Georgina didn't really think that far in advance." Andrew rushed through his words.

Bart shut his eyes without a word, letting the seconds slip by in silence. He sucked a deep breath in through his nostrils before speaking. "Damage control?" He asked, the pressure of his forced calm creating an almost palpable tension in the air.

"None so far," Andrew said. "She may or may not have been on birth control. She has a prescription. Whether she takes it as prescribed is another thing. I've only started digging through her files so far, but it seems she has plenty to choose from if we need a little help extorting her. She was definitely not a virgin. There is some questionable substance abuse. I have a few pictures, but at the rate the girl is going, it shouldn't take long to compile a nice blackmail package, if the need should arise."

"Good," Bart said simply, standing from his desk suddenly. "Is that it?"

Andrew nodded his head, already stowing his blackberry inside his briefcase. He was well versed in Bart's abrupt dismissals. He was halfway out the door when he turned back to face Bart with some parting advice. "You might not want to go over there right now," he said, easily guessing the older man's next move.

"And why is that?" Bart demanded, already slipping his suit jacket onto his shoulders.

"He's got a girl over there," Andrew admitted. "A woman, actually. And uh, you might want to hire a new Nanny. An ugly one. Or at least one that doesn't have a fetish for young boys." He hinted at the identity of Chuck's newest conquest before closing the door behind him on his way out.


	8. Chapter 7

**Author's Note:** This chapter is a little different in that it switches primarily to Chuck's point of view. I haven't decided whether or not this will be a permanent change or not. And I haven't decided whether or not I like this chapter. But, regardless, thanks for reading. And thank you, thank you, thank you to everyone who left feedback. You guys seriously made my day. It was very much appreciated.

Chapter Seven

Chuck Bass was sprawled comfortably on his back on the floor of the Archibald parlor. "Com'on, Nathaniel," he said. "Pass it already. You're smoking up the last of my stash." Chuck reached out and shoved Nate roughly, nearly toppling the boy that sat beside him.

"Fine, fine," Nate mumbled with the joint between his lips, taking one last hit before passing it to Chuck. For all its liabilities, being friends with Chuck Bass had its definite perks. Chuck had great connections. For instance, take the pot they were smoking. It was premium stuff, comparable to some of the best blends he'd smoked in Amsterdam last summer. The first joint they'd shared had done a great job of mellowing Nate out. It was the perfect escape from having to think about his fucked up family. Now onto their second, he was feeling sluggish and more than a little giddy.

"Could you please try to control your drool," Chuck deadpanned as he placed the joint to his lips. "I'd prefer not to swap spit with you, Nathaniel. You're not my type. I much prefer brunettes." His deep voice eased out without a hint of humor.

"So that blond you were fooling around with last weekend…" Nate trailed off with a grin, raising his eyebrows to his friend as he reached for the joint.

"Dear Nathaniel," Chuck drawled out lazily. "With enough Champaign, they all look like brunettes," he retorted, transferring the joint to Nate's outstretched hand.

"Hmmm," Nate mused. "From what I saw there wasn't enough alcohol in the world to hide the fact that she was a natural blond," he chuckled. "By the way, remember to lock the door next time. I'd prefer not to walk in on you and some random. The mental images alone..." Nate trailed off as he gave an exaggerated shudder.

"I can't be held responsible for what occurs in the heat of passion, Nathaniel," Chuck smirked as Nate passed him the joint.

"Dude!" Nate gave a disgusted groan. "I do not want to hear about you and any kind of passion," he laughed as he kicked Chuck.

"I'll have you know that…" Chuck trailed off as blur of movement caught his eyes and Blair Waldorf waltzed into the room unannounced.

She was a flurry of perfectly curled brown hair, a perfectly pressed school uniform, and blatant disapproval as she strutted over to where they sat. "And exactly _what_ do you think you're doing?" She huffed.

"Blair!" Nate exclaimed, his reflexes dulled. He quickly passed the joint to Chuck as he jumped to his feet. "We were just—"

"Smoking up," Chuck supplied when Nate was unable to complete his sentence. "Care for a toke, Waldorf?" The look of irritation that crossed her features only caused Chuck's smirk to stretch further across his face.

"Your parents leave for one week and you've let Chuck turn your parents' parlor into an opium den," she fumed, her hands perched stubbornly on her hips.

"You're not wearing any underwear," Chuck drawled out, his position on the floor and Blair's close proximity allowing him to gaze directly up Blair's skirt.

"I am so!" Blair protested as she clutched her skirt against her thighs and clamped her legs together. "God, Chuck, do you really have to be so disgusting?"

"Disgusting? I'm not the one going commando," his deep voice oozed sleaze effortlessly. "Am I interrupting an afternoon quickie with dear Nathaniel?" He questioned smugly, knowing the easiest way to ruffle her feathers was to question her virtue.

Blair fumed silently and decided her best tactic was to ignore Chuck. Instead, she turned to give her full attention to her boyfriend. "What do you have to say for yourself?" She asked Nate. "Your parents would be furious if they knew what you were doing? It's illegal. My future husband can't be a felon!" She was clearly distressing herself with this line of thinking.

"It was just a little pot, Blair," Nate tried to explain calmly and rationally, two words apparently not in Blair's vocabulary today.

"No," Chuck grinned suddenly. "Blair's right, Nathaniel."

"What?"Nate asked as he whipped his head around to face his friend. He must be having some kind of hallucination to think he'd actually heard Chuck agree with Blair. That never happened. The two were constantly at various stages being at each other's throat. Nate didn't even bother to keep up. And now they were suddenly saw eye-to-eye? Nate rubbed a rough hand over his face, trying to make the hallucinations go away. Fuck, what exactly had Chuck cut the pot with?

"No more pot, Blair. I promise," Chuck continued. Standing from his position on the floor, he ambled smoothly across the room, stopping in front of the wet bar. "Let's move on to something else," He suggested with a mischievous grin. "Why don't we sample a bit of the Captain's scotch? Scotch is legal."

"But consuming alcohol at fourteen isn't," Blair shot him down quickly.

Nate grinned at the idea, despite the disapproval written all over Blair's face and her tone. "Just a glass or two," Nate qualified. "Com'on, Blair. You drink Champaign all the time. Lecturing to us about drinking would make you a hypocrite."

Blair glared hatefully at Chuck Bass. He was a bad influence on her boyfriend. Nate had been so much easier to deal with when he didn't know any three syllable words.

Chuck grinned, mischief glinting in his eyes despite his dulled senses. He reached for the crystal decanter, pulled the stopper, and filled up two glasses with the amber liquid. "Bottoms up," Chuck said, lifting his own glass to his lips as he nudged the second glass towards Nate.

"This is a bad idea," Blair sighed, watching as he boyfriend and Chuck eagerly downed the potent liquor, resigned to the fact that her boyfriend and his best friend were complete and utter dumbasses.

***

"I am… perfectly fine," Chuck's deep voice drawled out unusually slow, his eyelids already half closed. It was a defense mechanism. If his eyes were half closed then the inside of the limo wouldn't spin quite so wildly before his eyes. "I'm not drunk," he slurred the words out unimpressively. "I'm fine," Chuck reiterated before his abnormally heavy head thudded ungracefully against the window of the limo before emitting a loud squelching noise as his cheek slid down the glass.

"I don't know, Chuck," Nate began uneasily, looking unconvinced by his best friend's reassurances. "You should probably just stay at my house, man. We can still go back, y'know? We could pick up some take out on the way back to soak up some of the alcohol. Me and Blair will—Chuck?" Nate stopped mid-sentence, frowning as he realized there was a good chance his friend wasn't still conscious.

Nate could vaguely recall listening to those stupid health awareness tapes at school, warning about the dangers of drugs and alcohol. At the time, the horrific acting had taken the edge off of the adverse health effects shown. It didn't seem quite as amusing now. If he had to take Chuck to get his stomach pumped, the shit would really hit the fan in his household. His mother would die from the embarrassment alone. And God knows what Bart Bass would do to him. Or Chuck, if he survived. Nate tilted his head towards Blair, who sat wedged in between the two boys in the limo. "Is he still breathing?" Nate asked, starting to get worried. The high he'd felt earlier was all but a distant memory now.

"I don't know," Blair snapped, annoyed at the entire situation. She had told both of the boys how stupid it was to dip into the Captain's supply of scotch. Repeatedly. Nate had heeded her warning, not even finishing a single glass of the liquor. Chuck, however, had made up for Nate's hesitation. He downed glass after glass, if for no other reason than to spite Blair Waldorf.

"Could you at least check?" Nate asked calmly, unruffled by her harsh tone. That was Nate, always mellow and laid back, with not so much as a strand of his perfectly groomed blond hair out of place. Blair never understood why he enjoyed smoking pot with Chuck. Nate generally seemed stoned and confused while completely sober.

Blair huffed in response, leaning slightly over in her seat to check on Chuck. The boy's face was pressed against the glass, his mouth hanging open in a most unattractive manner. "He's fogging up the window," she stated by way of an answer.

Unsatisfied with her assessment, Nate called out his friend's name loudly. "Chuck?" He reached across Blair, grasping Chuck's shoulder and shaking him roughly, dislodging Chuck from his uncomfortable position sandwiched against the window and causing him to slump into Blair.

"Ew!" Blair squealed sharply. "Get off, Chuck," she spat out, already shoving Chuck back towards the door of the limo.

The boy grinned smugly through his half-closed eyes. "Only if you promise to lend a hand," Chuck slurred out thickly as he made a vulgar jerking motion with his hand.

"Ugh," Blair wrinkled her nose in disgust. "You're vile," she told him as she leaned away from Chuck. "And you smell like Britney Spear on a binge. There's no way Bart's going to miss that."

In a matter of seconds, the smug look was wiped clean from Chuck's face and was replaced by a pained expression. "I don't feel so good," Chuck moaned, uncharacteristically pitiful and looking decidedly pale and tinted green.

"If you hurl on me, Chuck Bass, so help me god…" Blair seethed, trying her best to push her tiny frame as far away from Chuck as possible in the small vicinity of the Archibald limo. God, he was a direct descendent from the Vanderbilts. Why did he have such a small limo?

"Maybe some air will help. Roll down the window," Nate instructed. When Chuck made no movement, Nate leaned over Blair and hit the automatic window control, allowing a gust of cold evening air to infiltrate the interior of the limo.

"It's cold!" Blair protested shrilly, in the process of reversing the direction of the window.

"It's either puke or cold," Nate shot out. "Take your pick, Blair."

Her hand fluttered over the window control before she pulled away, defeated. "Fine," she relented, a firm pout resting on her features. "We're almost there anyway," she grumbled as the limo began to slow and pull to the curb of the Palace hotel.

Chuck's hands grappled clumsily with the door handle, pushing the heavy door open even before the limo could come to a complete halt. In a flash of movement, he leapt from the still moving limo and onto the pavement of the sidewalk.

"Chuck!" Both Nate and Blair yelled at the same time.

Chuck's already precarious sense of balance was amplified by the leftover shock of jumping from a moving vehicle and he took several stumbling steps before managing to catch his balance. He spun around, a cocky grin on his face. "Told you I was fine," he slurred out his words. Turning from them, Chuck took three more staggering steps before he found himself sprawled out on the pavement that had formerly been beneath his feet. Gravity was tricky some days.

"Chuck!" Blair squealed again before erupting into undignified giggles as she and Nate scrambled from the now stationary limo. "Are you—Oh, that was just revolting," Blair's mixture of amusement and concern were quickly replaced with repulsion as Chuck watered the hotel shrubbery with the mostly liquid contents of his stomach.

With his entire afternoon's activities decorating the bushes, Chuck turned his head pathetically and wiped his mouth with the back of his hand. "Next time… I'll aim for you, Waldorf," he replied sourly as he lumbered to his feet.

Despite expelling the majority of the alcohol he'd drank that afternoon, Chuck still swayed unsteadily on his feet, looking every bit as rumpled and worn as he felt. His eyes were blood shot, his tie hung loose around his neck, and his hair was in a state of disarray that only Chuck Bass could pull off.

"You look like crap, Chuck," Nate observed. "Com'on, let's go back to my place. You can't possibly think you can sit through a four course dinner with Bart and the new mistress. You can barely stand on your own. Let's go, man. He'll kill you if he sees you like this. And then he'll kill me for letting you get into the Captain's scotch," Nate pleaded with his friend. Bart Bass was a scary guy. Nate, who generally liked to avoid confrontations, preferred not to find himself quickly at the top of Bart's shit list for dumping his very intoxicated son on the front steps of the Palace hotel. "Get back in the limo."

"Nate's right," Blair pitched in. "You look and smell like a wino; you can barely stand up; and," she wrinkled her nose in disgust. "You have vomit on your tie."

Chuck took a deep gulp of air before turning from the pair, the churning contents of his stomach making another appearance. Funny, he really didn't remember it burning this much on the way down. "I'm fine," he protested weakly, shooting his hand out to steady himself against the brick wall of the hotel. Chuck Bass never backed down from a challenge. And besides, the danger of upchucking into his salad was minimal considering there was surely nothing left in his stomach by now. With his free hand, Chuck jerked roughly at the tie around his neck without much success.

"You're going to strangle yourself," Blair snapped as she walked briskly to where Chuck stood. "Quit, quit," she swatted his clumsy and rough hand away from his tie. "Let me do it," she ordered as she easily slipped his tie from his neck before straightening his collar. "If you're going to insist on doing this," Blair continued in a much softer tone. "At least get some breath mints from the concierge." She advised him as she brushed her fingers through his hair in attempts to bring some order to his messy hair. After a few minutes of fussing without so much as a squeak of protest from Chuck, Blair took a step backwards to admire her handiwork. "There," she said. "Considering my starting material, I'd say that you look half-way presentable." She smiled as she practically pranced back to Nate's side.

"Just don't talk much," Nate advised warily.

Chuck Bass keep his mouth shut? There was a greater chance of Blair losing her virginity in a moving vehicle.

"Yeah, yeah," Chuck brushed off their comments and continued to gulp down deep lungfuls of the cold evening air, anything to keep his churning stomach from forcing its remaining contents in reverse. He really shouldn't have had that last drink. If he hadn't been concerned with spewing chunks, he would have scoffed at this thought. That wasn't true. He really shouldn't have had any of the drinks, much less the last four drinks. And he really shouldn't have done it after sharing a bowl or two with Nate. "I'm fine," Chuck muttered again, his tone lacking any amount of convincing.

"Good luck," Nate said, clapping Chuck on the back before turning to leave.

"Call if you need bail money," Blair called out over her shoulder cheerfully as she and Nate headed back to the awaiting limo.

"Bitch," Chuck muttered under his breath, fighting the corners of his mouth from twitching up into a smile.

***

Chuck Bass swore under his breath as the elevator stopped, yet again. It seemed every stop ended up in an even exchange of passengers, with just as many people getting off as were getting on. It was as if the entire universe was conspiring against him. And the constant lurching of the elevator as it stopped and started again was agony for Chuck's unsettled stomach and swimming equilibrium. In fact, the only thing that that stood in the way of him slouching into the puddle on the floor was the death grip he had on the metal bar that ran the circumference of the compartment. And though sharing his bodily fluids with the rest of the passengers might have vacated the elevator quickly, Chuck wasn't quite ready for that kind of humiliation.

At the twelfth floor, when the last remaining passenger had vacated the elevator, Chuck gave a sigh of relief as his head thudded against the wall of the elevator. It was short lived, however, when the elevator made another sudden stop on the fifteenth floor. "Jesus fucking Christ," Chuck roared into the elevator, his stomach lurched violently once more. The doors opened to reveal an overweight, middle aged woman dressed in tacky tourist attire. Her glowing smile quickly wilted under Chuck's murderous gaze. "No," he practically spat out as she took a step to enter the elevator. "This elevator is out of order," he slurred out. "Take the stairs. It looks like you could use them," he sneered as he repeatedly stabbed the 'close door' button. Apparently his point was made clear, because though the woman huffed in indignation, she stepped back from the elevator.

Chuck swallowed hard as the elevator lurched to life again, this time smoothly traveling upwards until it reached the penthouse suite. He stumbled out of the elevator as soon as the door opened. Gravity had other ideas, and Chuck was forced to grab the wall as he nearly fell to the ground. If he was going to pass for semi-sober, his motor skills were going to need some gross improvements. Taking a deep breath, Chuck tried again, walking quickly as his lead-filled legs would take him. The quicker he walked, the less noticeable his staggered gait was.

Chuck was so intent on keeping his feet, instead of his ass, planted on the floor that he didn't notice the woman standing in front of him. That is, he didn't notice her until he'd plowed into her, nearly knocking the both of them to the ground.

"Charles," Bart greeted him coolly as he glanced pointedly to his watch. "How nice of you to finally join us."

"Sorry," Chuck muttered his apology to both the woman and his father. At this point in his life, Chuck knew better than to make excuses. Bart had little patience for them. It only made things worse. And tonight, he would rather not tempt fate by opening his mouth any more than necessary. The goal was to just survive until the second course and claim illness for an early departure. The woman being present just made the plan all the more perfect. With a female companion present, Bart wouldn't want to linger.

"I see you've met Candy," Bart said, gesturing to the woman who looked so young that she could have easily passed for Chuck's older sister.

"Stacey," the woman corrected, though she strangely didn't seemed embarrassed by his slip.

Neither did Bart, for that matter. "Yes," he said simply, not bothering to correct himself. "Come, let's eat. The first course is getting cold."

***

Chuck's vision was hazy and he fought to focus, to look interested in the blurred words Bart and his bimbo of the week were speaking. However, instead of picking up the conversation, Chuck could feel his eyelids being pulled closed by an unseen force. It was a fight against gravity, and he was losing. Miserably. His head began to dip, tipping his head forward. As Bart's words were all but an indistinct buzz in his ear, Chuck's nose inched closer and closer to the bowl of steaming soup that sat in front of him.

Bart paused for a moment, mid-sentence, his eyes suddenly narrowing at his son. "Charles?" He asked, slightly confused at the sight of his son's nose nearly touching the untouched first course. That was when he heard it, a faint though distinct snore blew past his son's lips. "What in the hell are you doing?" His voice boomed, letting his soup spoon clatter noisily to the table.

Chuck flinched, jerking his head upward just moments before he would have face planted into the soup bowl. "The soup," he slurred. "It smells exquisite," he recovered quickly, trying his best to focus his bloodshot eyes on his father and the companion of the week.

Chuck grabbed his spoon for an excuse to take his eyes off of Bart. Though the idea of putting anything in his quivering stomach was nauseating, at best, Chuck managed to fill his spoon with soup and a somewhat successful trip to his mouth. He swallowed hard, forcing the food down his throat.

"How is the soup, Charles?" Bart Bass asked innocently, picking up his own soup spoon again. Bart Bass was nothing if not observant. From the moment Chuck had stumbled out of the elevator, Bart had been well aware of exactly how inebriated his son really was. The lingering smell of perfume and mint masked alcohol had been his first indication. The second was that, despite Candy's plunging neckline, his son had barely glanced at the woman's cleavage. And the final indication was that his normally loquacious son was replying in monosyllable answers that were barely more sophisticated than grunts. Now Bart could have raged into a fit as soon as he'd caught a whiff of the alcohol that was practically seeping out of Chuck's pores. He could have yelled, made a scene, and sent Chuck to his room. But then Bart would have missed the opportunity to teach Chuck a lesson that would make him think twice the next time he decided to hit the bottle just before a scheduled family dinner. Besides, struggle builds character. Given his son's luxurious lifestyle, a little discomfort would do him good.

"Good," Chuck answered through gritted teeth. God, why did his father suddenly take an interest in his opinion on tonight of all nights? The more he opened his mouth, the greater chance of something other than words coming out. If he got through this dinner alive, Chuck was never drinking again. Never ever.

"So, Charles, how was school today?" Bart tried again to restart the conversation.

"Fine," Chuck answered curtly, looking decidedly more pale and clammy with every bite of soup he took.

"Oh," Bart smiled stiffly, "I'm sure you can do better than that. Why don't you tell uh," he faltered momentarily as he clearly forgot his companion's name. "Why don't you tell _us_ about your upcoming science fair project? I'm assuming you've already started given that it's due on Monday."

God must surely hate him, Chuck thought darkly as he tried not to glare at his father. Couldn't the man let him sober up in peace? He hadn't been this attentive since Chuck had broken his arm in the first grade. "Hydroponics," he muttered after swallowing down the bile he felt inching up his throat.

"Hydroponics?" The blond bimbo asked. "What's that?"

Bart smiled in response to her question. Who knew his nightly companion would prove to be useful outside of sex?

Chuck blanched at the thought of how many words it would take to describe the project he and Nate had been working on during the past few weeks. Glaring at the woman just reinforced his dislike for blondes, even if the woman's particular shade of blond likely came from a dye packet. "Growing plants without soil," Chuck blurted out with some difficulty. He didn't mention the fact that he and Nate had been growing _Cannabis sativa_, and that fact alone was the only reason he'd actually started the project.

"You can do that?" The woman seemed genuinely impressed. Bart certainly didn't pick his companions for their intellectual prowess.

Chuck nodded his head, his churning stomach thankful for a question that didn't require speech.

By the time Chuck had managed to choke down the remains of his soup, he was half-way convinced he could survive the entire meal. He might have even been feeling a little cocky when the wait staff appeared and whisked away his soup bowl only to replace it with a large plate of sliced filet mignon.

One glance to his plate was enough to send Chuck's stomach into overdrive. The meat was rare, with its pale pink juices pooling underneath the meat and seeping across the plate. He immediately averted his gaze and sucked in a deep breath. That had been a mistake, and ultimately what had done him in. The deep breath sent the fragrant smell of the food flooding into his system. Chuck gagged, quickly clamping his hand to his mouth in attempts not to projectile vomit all over the table. "Excuseme," his muffled words ran together as he jumped up from his chair and stumbled towards the nearest available bathroom.

"What's the matter with him?" The blond asked, genuinely confused as to Chuck's quick escape.

"I haven't the slightest clue," Bart answered, the threat of a smile tilting the corners of his lips.

"Is he okay?" She asked, rising slightly from her seat. "Aren't you going to check on him?" She asked.

Bart simply shook his head. "He'll be fine," he answered before taking in the generous cleavage his companion was sporting. "But why don't we get a private room tonight?" Bart smiled stiffly, "in case whatever Chuck has is contagious."


	9. Chapter 8

**Author's Note:** Many apologies for how long this has taken me to churn out. I'm in the process of writing my dissertation as well, so unfortunately writing for fun gets shifted way down on my things to do list… right down there with eating and sleeping. As always, all forms of feedback are appreciated.

**Chapter 8**

Bartholomew Bass didn't like surprises. Surprises were wild, dangerous, and unpredictable. Like a firecracker throw up into the air, once the fuse was lit there was no controlling its path of flight. A surprise meant that every single plan and contingency plan (and contingency contingency plan, if he was being honest) Bart had spent hours formulating had been, to put it bluntly, shot to shit. A surprise meant that the situation had suddenly morphed from carefully controlled to absolute chaos. And chaos wasn't controllable. And there was nothing in the world that made Bart Bass squirm more than the inability to control something.

After all, Bart's entire life had been structured around control. A controlled situation could be exploited. And Bart had exploited every situation and secret he came across. Some people might call his methods unscrupulous. Those people were generally right. But good ethics didn't build you a multibillion dollar company from scratch. Bart's endless ambition and hard work had been a good start, but it was his willingness to get his hands dirty that had allowed him to amass such wealth, prestige, and fear. Friendships, relationships, they meant nothing. Exploitation and a flexible set of morals, however, were the quickest way to the top when one was born with a blue collar rather than a silver spoon.

But the problem with knowing everyone else's dirty little secrets was that it often distracted from one's own faults, shortcomings, and misdeeds. After all, neglecting your son was hardly a juicy piece of gossip when you lived in a zip code that practically invented sandal. And Bart knew everything. He knew who was sleeping with whom. It still amazed him that, in the Upper East Side, listing one's sexual partners was like playing five degrees of separation. Technically speaking, it was like one gigantic orgy of crisscrossed lovers. Bart knew all about secret sexual orientations and perverse sexual proclivities of his frenemies and neighbors. Wealth most certainly did not always bring sound judgment or even a good sense of discretion. Bart knew credit scores, bank balances, and every last whisper of sandal, corruption, and greed. He knew who was married in name but nothing more. Bart even knew which children whose paternity was a game of Russian roulette with the gardener, the personal trainer, and the pool boy. Business mergers, tax fraud, off shore bank accounts, bankruptcies, Bart Bass knew it all. At least in theory.

Knowing a person's actions didn't always bring insight into that person's character. Never was there a more frustrating example of this than Bart's own son. Charles Bartholomew Bass was a sink of contradictions and unanswered questions. Even after raising the boy as a single father (never mind the fleet of nannies, tutors, and maids that did all of the dirty work), Chuck was as transparent as marble. And no amount of intel gathered on the boy could ever seem to change that. Not that Bart let this dissuade him. Bart had folder after folder compiled on the boy before he'd even hit puberty, but it only seemed to contribute to the frustration.

His son was like him in many ways. Bart didn't need a private investigator to tell him that his son clung to control like a bulimic to a toilet seat after a heavy meal. Like father, like son. And on the outside, Chuck was every bit as cold, calculating, and callous as Bart, if not more so. Had Bart mastered a facial expression that extended beyond a disapproving frown or an icy glare, he might have beamed with pride at how well his son shielded himself from others. Bart also knew that his son was considered a loner, calling only a select few people his friends. Friends were liabilities, in Bart's opinion. This was precisely why Bart never bothered developing relationships that didn't result in a business acquisition or a decent blow job. Chuck had been all of nine or ten years old when Bart had taught the boy of the cold and cruel nature of the world when your last name was Bass. Never trust anyone, he had told the wide eyed boy. There's no such thing as altruism in the Upper East Side. Fuck up, and someone would only be glad to share your mistakes with the world. There are only three categories of people necessary in a man's life, Bart had explained to Chuck. Business associates, future business associates, and whores. Anything beyond that just complicates matters.

But where Bart had used many of these personality traits to his benefit, furthering himself and his company, Chuck squandered them. The boy would have flashes of hard work, and it was truly impressive. But, unlike Bart, Chuck felt he had nothing to prove to anyone. The boy was more than happy to drop the Bass name to get his way, but did nothing and showed zero interest in adding anything other than a rap sheet to the family name. It was a waste of talent. And so Bart pushed and challenged the boy on a regular basis, but it never seemed to help.

While Chuck's personality often mirrored Bart's, he was his mother's son in every other way. It had taken Bart years to be able to look at the boy without cringing. Even now, Bart often avoided Chuck's eyes. They were the precise shade of deep brown as Misty's. But, unlike Misty's eyes, which had always been bright, bouncy, and full of life, Chuck's eyes were tragically dark and withdrawn. Bart knew his son was deeply unhappy. But because Bart was much more practiced in giving stern disapproval rather than fatherly advice, he said nothing to the boy. And as Chuck grew older, he seemed to dip deeper and deeper into unhappiness.

Bart turned his back on Chuck's expanding methods of escape, letting the boy attempt to drink, snort, and fuck away the misery. He indulged Chuck in open access to alcohol, and Chuck repaid him by developing a drinking habit that rivaled a middle-aged man. Bart turned a blind eye to the premium week Chuck openly smoked. And, if need be, Bart paid others to do the same. He looked the other way to the rainbow of pills his son popped. Snorting cocaine, well that was just a phase that everyone went through. Even stuffy Bart had once been young and lived through the 60s. As for Chuck's preoccupation with hookers, he was a teenage boy with an overactive libido. Simple. But as much as Chuck attempted to hide behind a chemically-induced haze, it never seemed to help.

Bart couldn't remember the last time he'd seen a real smile from his son. The boy didn't laugh, didn't smile, and rarely uttered anything more than lewd innuendo or a sarcastic comment. But when Bart glanced up from his morning paper at the sound of Chuck's shoes against the kitchen tiles, he was greeted by a hesitant smile tilting Chuck's lips. And Chuck's eyes, formerly dark and dull, were brighter somehow. Bart couldn't help but stop and stare. At that moment, Chuck looked so incredibly like his mother that Bart's heart thudded wildly in his chest. Had Chuck not been busy spreading a thin layer of jam over his toast, Bart was sure he would hear. Swallowing hard, attempting not to draw attention to himself, Bart forced his eyes back down to his paper.

Chuck, well accustomed to Bart's irritation at being interrupted while he browsed the morning paper, kept his morning greeting short and polite. "Father," Chuck greeted him with only the briefest of glances in Bart's direction before reaching for some juice. And while Chuck's smile had disappeared momentarily when he'd greeted his father, it began to tug at the corners of his mouth once more as he sat down at the breakfast table.

Bart was floored. Was Chuck… happy?

Shit, how much was this going to cost him?

Bart cursed himself silently for immediately thinking the worst, though he didn't banish the thought from his mind completely. He sat down the paper, studying Chuck without the shield of his morning paper to hide behind. "You're up early," Bart commented in what he hoped was a casual tone. "What are your plans for today, Chuck?"

Chuck looked like a deer caught in the headlights of a pick-up truck, his mouth still slightly bloated from the toast he'd been unceremoniously shoving into his mouth. The boy reached for his juice quickly, washing down the remains of his breakfast before answering. "Nothing special," Chuck answered evasively as he shrugged his shoulders. Just when it seemed as if that was all the answer Bart was going to get, Chuck spoke again. "There's a party tonight," he said. It was subtle, but his words were not quite as polished and arrogant as usual. Bart noticed immediately. Chuck licked his lips and Bart could almost feel the boy's nervousness. "A birthday party," he clarified. "I need to pick up a gift."

Bart studied his son silently. Never once had his son asked permission to spend money. With a rather healthy allowance deposited in his bank account every week, Chuck had never had reason. "You need money?" Bart asked. A loud sigh blew past Bart's lips as he shook his head in disapproval. "One day, Charles, you're going to have to learn to manage money," he scolded. "An excess of income won't last long if you can't master that."

"It's not that, father," Chuck said quickly, holding his palms up in defense. He opened his mouth to speak but words failed to follow immediately. After a long pause, he began again. "This birthday party," he said, selecting his words carefully. "I'd like to get a specific gift. But… I don't—I'm not sure if…" the boy was growing flustered like Bart had never witnessed. "I need money," he blurted out finally, obviously abandoning whatever he'd been about to ask Bart. "I spent all my allowance already," Chuck stated in a tone that matched his facial expression, defeated.

When had he become so unapproachable to his son that the boy would rather take criticism than have a real conversation with his father?

By force of habit, Bart frowned as he studied his son. "And what is this specific gift that you have in mind?" He asked, attempting to re-open the conversation.

Chuck's jaw flexed under his clenching teeth and his eyes refused to meet Bart's. "I'd rather not say," he replied simply, all remains of his former cheery attitude wiped clean from his face.

Bart stayed silent for a moment, letting his eyes take in everything about the boy in front of him. Deciding not to push the subject, Bart nodded his head. "I'll arrange a transfer with Anthony. Call him later and let him know how much you need." Bart hesitated momentarily. "And Charles," he said sternly, unable to stop himself. "If I find out you're using this money for drugs or whores, don't think I won't cut you off until you learn this money is a privilege and not a right."

Chuck nodded his head glumly, pushing his chair back from the table with a loud scrapping noise. "Yes sir," he answered simply, already seeking an exit.

Bart watched his son leave, waiting until he heard the elevator doors close before he pulled open his cell phone and pressed the first number on speed dial. "Andrew," he greeted curtly before launching into his request. "I want you to keep a close eye on Charles. He's up to something," Bart stated, his tone flat. "And I want to know what it is." Without waiting for an answer, Bart slapped the phone shut and picked up his morning paper once more.

***

"And Chuck?" Bart asked Andrew, his stern face blank of any emotions even at the mention of his only son. At Andrew's hesitation, Bart sighed deeply and pinched the bridge of his nose. "What has he done now?" His tired voice inquired. Perhaps he hadn't jumped to untrue conclusions this morning at breakfast. "I'm almost positive it can't be worse than anything he's already done. Are we talking jail time? Hookers? Drugs?"

Andrew shook his head. "No, no," he said, trying to clarify the misunderstanding. "It's nothing like that. Chuck has been surprisingly good the past couple of weeks. Um, it's just… the Waldorf girl, Blair."

"What about her?" Bart asked warily. The Waldorf's were old money. Harold had been one of the very few people Bart would have ventured to call a friend.

"It's nothing bad. At least I don't think it's bad." Andrew explained.

"Would you just spit it out," Bart's temper flared.

"She and Chuck had sex in the back of the limo last night."

This caught Bart off guard. "Blair Waldorf," he mused, the stern expression on his face suddenly vanishing under clear astonishment. "But I thought she was engaged to the Archibald boy?"

"Not exactly," Andrew took a deep breath as he pulled a folder from his briefcase. "I still believe that was the plan heading into last night. I bought these off of an associate of mine." He said, pulling several 8x10 shots of the Archibald family out of a folder. "It appears there was something of an altercation at the Waldorf residence last night," Andrew described the scene politely as possible.

Bart's gaze lingered on a shot of the Captain slugging his son on the street. The photo comforted him somewhat. At least his relationship with Chuck had not been reduced to physical blows.

"The Captain was arrested, as you already know, for possession. Of course that was just a ruse to nail him on much greater charges, embezzlement and fraud. It seems that Nathaniel and Blair broke up in the aftermath." Andrew explained.

"Hm," Bart made a noise deep in his throat, catching sight of several more sets of 8x10 photos in Andrew's hand. "So she went to Victrola to see Chuck?"

Andrew nodded his head as he passed another set of photos to Bart. The first was a shot of Blair exiting the Bass limo in front of Victrola. The second photo showed Chuck's obvious confusion. "They spent the evening—"

"Did he drug her?" Bart interrupted.

"No," Andrew shook his head. "Your son behaved himself, much more so than I've ever seen in the past. Nothing was slipped into her drink. He barely even touched her while they were in public."

"While they were in public?" Bart repeated Andrew's words slowly, an eyebrow raised. "So he raped her in the limo?"

"I—uh," Andrew shook his head again. "I'm fairly certain it was consensual," he said, sliding another set of photos to Bart.

Bart flipped through the pictures. The limo parked outside of Blair's house. Chuck, giving Blair his hand to pull her from the limo. Chuck's leering grin and Blair's shy smile. Chuck, leaning against the limo and watching her walk from him, the beginnings of a smile tilting his lips. Bart's brow furrowed in concentration. This he had not been expecting. His son hadn't been attempting to squeeze more money out of Bart this morning. He'd been trying to ask Bart for advice… advice on a girl. Why did he always expect the worst from his son?

Because his son was a startling reminder of himself.

"Blair Waldorf," Bart began as the pieces began to fall in place in his head. "Tonight's her birthday party, isn't it?"

"That's correct," Andrew affirmed.

"And that's where Chuck went this morning. He was buying her a gift." Bart stated, no longer asking questions.

"An Erikson Beamon necklace," Andrew added.

"And he's with her now?" Bart questioned.

Andrew nodded his head, "he is."

Without thinking, a small smile graced Bart's lips awkwardly. After a long moment of silence, Bart glanced up, seeming as if he'd almost forgotten Andrew was still in the room. "That'll be all, Andrew," Bart dismissed him gruffly. "Oh, and Andrew," Bart called out once Andrew had reached the doorway to Bart's office. The man turned around, facing Bart expectantly. "Drop the tail on Chuck," Bart ordered. "Give him some privacy."


	10. Chapter 9

**Author's Note:** Many apologies to anyone actually following this series. My life doesn't extend far beyond the lab these days. That hasn't exactly left an abundance of time to write for pleasure. Anyway, I just have a few more months to go before I'm done. Can't wait. In the mean time, since I can't get the next chapter I'd intended to publish quite to my liking, I decided to interject with some fluff. The world needs a little more Happy!Chuck.

There was a boyish flush to his cheeks as his eyes fixated on the sliver of pale skin sandwiched between the hem of her pleated skirt and her stockings. Chuck Bass swallowed hard, trying in vain to divert his attention elsewhere. But the inane droning of the balding and bespectacled teacher in front of them held little interest in comparison. Within seconds his eyes snapped back to her, and he barely suppressed a groan when she shifted in her seat, causing the material of her skirt to ride up higher on her thighs.

For all the charm, poise, and perfection that practically radiated from Blair Waldorf, she was a shark. Few people understood the amount of shrewd and calculating scheming that went on behind her large, doe-like brown eyes. So while most people assumed she was engrossed in the day's lecture, leaning forward in her seat, pen in hand, and eyes closely following the rambling little man in front of the class, Chuck knew better. She was teasing him, exploiting her knowledge of his weakness for her own personal gain.

Chuck Bass loved her thighs. It was odd, really. He'd never considered himself to feel anything other than ambivalence towards women's thighs. He'd seen then in all shapes and sizes, and it never seemed to make much of a difference. They had always been just a minor stop along the way to his final destination. But Blair's thighs were something of beauty. Smooth, shapely, but not so overly muscular that he felt inadequate for his own slothful ways. He worshipped her thighs just as much as the stockings that inevitably adorned them. He could imagine them wrapped around his torso or looped over his shoulders. Either scenario was fine by him. Maybe both.

The tingling warmth that had tinted his cheeks had now worked southward, tickling his stomach with a flurry of fluttering before settling with a pleasurable pulse in his groin. Chuck shifted uncomfortably in his seat and, as casually as possible, folded his hands over the impending tent developing just under his palms.

His movement attracted her attention. One quick sideways glance in his direction, and a victorious smile was practically embedded in Blair's features.

That bitch!

Did she not know who she was dealing with?

He was Chuck Bass.

Chuck-fucking-Bass didn't get one-upped, especially not publically!

"Oh god," Chuck gave a deep growl and his eyelids fluttered closed momentarily as Blair, taking advantage of yet another of his weaknesses, had pulled her hair off of her shoulders into a messy bun.

That bitch with the heavenly thighs, Chuck mentally corrected himself.

The teacher that had been nothing more than background noise to the porn-like scenarios playing in Chuck's head suddenly appeared in front of him. "Mister Bass," he chastised, "is there something you'd like to share?"

"Afternoon prayer," Chuck answered in his usual drawling tone without missing a beat. "It's private."


	11. Author's Note

I've had a few inquiries as to whether I'm continuing this series or not, so I thought I'd do a mass communication instead of answering each person individually. The quick answer is: yes.

The caveat to that answer is that the update might not happen very quickly. I have most of the next chapter written, but since I'm currently studying for the MCAT I don't have a whole lot of time to write/edit. My aim is to have an update posted between now and June. After June, my life gets a lot easier and I'll have more time to write… barring that I don't totally flub the test.


	12. Chapter 10

Chapter 10

Blair Waldorf was a princess in every sense of the word. She could be whiny, childish, needy, and insecure. Incredibly spoiled didn't even begin to describe her. Worst of all, she continually obsessed with her life fulfilling a checklist of storybook perfection, no matter how badly she had to warp her perception of reality. But while no one could deny that Blair was a princess, Chuck Bass could never be confused for the golden prince Blair had pined over since birth. Hell, he couldn't even pass for a noble white knight, just waiting on the fringes to swoop in and rescue his fair maiden once the golden prince turned out to be a complete toad. Chuck's rescue plans, though plentiful and sometimes well intentioned, were based on scheming, ulterior motives, deceit, and, more often than not, blackmail. It was hardly a checklist for the makings of a hero. No, with his dark features, wicked smirk, drawling tone, and questionable moral, Chuck bore far more resemblance to the dark and dangerous villains of fairy tales than he ever did to the goodness and light of any make believe protagonist. Unfortunately for Chuck, happily ever afters most definitely did not apply to the antagonists of fairy tales.

And so while the villain may fleetingly get the girl, she was not his for the keeping.

Chuck had long since accepted the fact that everything good in his life inevitably fell apart. It was always a case of _when_, rather than _if_, his happiness would bite the dust. Like trying to hold water in his cupped hands, it trickled out from between his fingers no matter how tightly he tried to retain it within his grasp. It was inevitable, and, even at sixteen, Chuck understood this. Unlike his best friend, Chuck knew better than to ever think happiness of any kind was due to him. That's what happened when you didn't grow up with the protective bubble of Anne Archibald to shield you from anything even remotely unpleasant. But the month Chuck had spent with Blair had almost been enough to make him forget. That just made the fall so much worse.

And so Chuck sat on the roof of the Palace hotel, decompressing with his two favorite mood altering companions, the finest hash in Manhattan and a bottle of aged single malt.

There were few people in the world who understood Chuck's fascination with rooftops. It was a simple explanation, really. Living in New York had a multitude of benefits. The social scene was unrivaled. It was the pinnacle of culture and shopping. The food, both in terms of extravagance and diversity, was unparalleled. It also helped that, in New York, the Bass family name was a ticket to getting Chuck whatever he wanted whenever he wanted it. Even so, living in New York, particularly in the hovering and gossipy neighborhood of the Upper East Side, made escape nearly impossible for someone like Chuck Bass. There was always a chance of being seen by someone he knew or, worse yet, someone who knew his father. And though Chuck specialized in flying under the gossip radar of detection for most of the Upper East Siders, he'd yet to figure out how to escape the unrelenting scrutiny of his father.

The great, powerful, and all knowing Bart Bass, Chuck thought with a contemptuous sneer.

Any chance Chuck did have for privacy was ruined by the ever-increasing depths of his father's paranoia. Bart was probably the only man in the world who would rather hire a tail for his son in lieu of having an actual two-sided conversation with the boy. But even Bart's PI has his limitations. Thankfully for Chuck, probing for weaknesses was among his many talents. It hadn't taken long, really. Soon after Chuck discovered the tail his father had on him, he also realized that roofs provided the perfect hiding place. With only a singular exit leading to and from the hotel to the rooftop, the roof of the Palace hotel was among the very few places that Andrew Tyler couldn't follow him. And so, even if it was only for a few hours at a time, Chuck could escape and at least dream of some semblance of privacy.

Of course that was just the surface of Chuck's fascination with rooftops. There was more, much more. It was never enough for Chuck to simply be on the roof. He needed to be perched on the very ledge. While it was true that any location, even those seating positions that were a safe distance from the dangerous ledge would offer most of the benefits that a rooftop had to offer. There would be privacy. The view of the Manhattan skyline at sunset would still be just as spectacular. The breeze would still be able to ruffle his hair; and the warm sunshine would still beat down in delightfully warm pulses on his neck and shoulders. In short, all of the relaxing, therapeutic benefits of being alone on the roof would be there regardless of where he sat on the roof.

But where was the thrill in standing so far away from the ledge, all safe and sound?

He was a Bass, and Bass men never did anything halfway. It was all or none. That was precisely the reason why, despite the expanse of much safer seating arrangements looming behind him, Chuck Bass perched on the ledge of the roof, dangling his expensive loafers over the open air of the city that was several dozen stories below him.

At least that was the very pretty lie to cover up the very ugly truth.

Chuck sat on the ledge because, one day, he would finally find the nerve to do what the world seemed to be tempting him to do since birth: jump. Just a few careful inches in the wrong direction and Chuck would be eating concrete. Physics, a course Chuck had bribed and cheated his way through, suddenly made sense. Abstract ideas, such as the force of gravity and inertia, were made so much easier with real world application. Neglecting air resistance, it would take approximately 32.5 seconds for him to hit the sidewalk.

Bart would be practically brimming with pride to know that Chuck was finally putting his overpriced private education to good use.

If, by some miracle, he survived the 55-story drop, it would only take a few extra minutes for him to lose the quart of blood necessary to send him into irreversible, systemic shock.

See, that's the subject of biology in real world terms.

And this was only if popular opinion proved to be incorrect. Chuck Bass didn't have a heart. No heart? No blood, no mess, no wait. It was simple, clean, and highly effective.

But he was a coward today… the same as every other day of the past sixteen years.

While Chuck sat recklessly on the ledge, his weight remained shifted towards the interior of the rooftop. Safe and sound, just like the coward he was. His aversion to pain, especially that of the physical kind, kept his morbid fascination with suicide in check. But it didn't prevent him from tempting fate. With enough pot and alcohol coursing through his system, it would only be a matter of time before he simply slipped and the decision would be made for him.

Always the coward's way out.

Chuck sighed before taking a heavy drag from his joint, lazily pulling the pungent smoke down into his lungs as he rhythmically swung his legs. His shoes thudded harshly against the bricks of the building on each downswing of his legs, roughly scuffing the fine Italian leather. The shoes would inevitably be scratched and ruined beyond repair. Chuck knew this. But after the day he'd had, he just couldn't bring himself to care.

Indeed, it was a low day when not even high fashion sparked a flicker of interest in Chuck Bass.

He gently flicked the ashes of his joint, sprinkling the city below with the charred remains of his joint. Simultaneously, his other warm swung around his body, bringing a half-filled glass of scotch to his lips. Yes, it was _that_ kind of day… week… year… fucking lifetime. A joint chased by scotch. And if Bart hadn't banned him from using the Bass jet as punishment and his god damn dealer hadn't been sunning it up in Fiji, Chuck would have added a little blow to the equation just for good measure. After all, what good were the five senses if they couldn't all be put to good use?

But the two depressants would have to do for now. So Chuck chain smoked his joints and shot some of the world's finest scotch like cheap whiskey, in deep, glass emptying gulps that burned as they washed down his throat. And, little by little, he happily let the hazy fog of pot and alcohol dull his overly analytical and relentless brain. Numb, number, numbest. So what if Bart had blocked his usual exit strategy? The illusion of escape was almost as good as the real thing. And it was still much more preferable than the fractured mess his life had become. And what a fine mess it was.

His father had essentially disowned him.

His best friend hated him.

And the girl he'd risked that lifetime of friendship over, the one who made his heart stutter in staccato and his stomach flutter? Well, she viewed him as a heartless villain unworthy of her time. She'd made it all too clear that Chuck wasn't even second best to her dear Nathaniel. He wasn't even her last resort. Simply put, he was a brief detour, made by mistake, and not a final destination.

Story of his mother fucking life.

After sixteen years of stern disapproval, Chuck should have been used to Bart's obvious dislike for him. Even so, being exiled from the family suite had been one of the lowest points of Chuck's life. Sure, he had openly mocked the idea of having a functional blended family with the van der Woodsens. But it had been tolerable. Okay, so maybe it had been even better than merely tolerable. It might have even been nice. After all, a dysfunctional blended family with the van der Woodsens was much better than no family at all. And anything was better than the loneliness of life alone with Bart.

Besides, Serena's disproportionate responses to his lewd teasing were quickly becoming the highlight of his day. And Eric, for all his wide-eyed innocence and sage wisdom, was actually fun to be around. Lily was no Stepford wife, but she had put a little extra effort into playing Mommy since they'd united households. It had been a welcomed change to have a parental figure that didn't cringe at the mere sight of him. And even cold and calculating Bart appeared to have softened a miniscule amount. But, as with any semi-good thing in Chuck's life, it didn't last.

There was no such thing as being innocent until proven guilty in the relentlessly judging eyes of Bartholomew Bass. Without so much as a shred of evidence, Bart had convicted Chuck of needlessly tormenting his future step-sibling and sentenced him to solitary confinement in 1812. All because the blond princess of redemption had opened her disproportionately large mouth and squawked, proving yet again that the few brain cells that rattled around, cold and lonely, in her skull functioned far behind her ever gaping mouth. If Chuck had ever been even remotely uncertain as to where he stood with Bart, that moment had clarified everything about their relationship… or the complete lack thereof.

Chuck shouldn't have been surprised. Had there ever been a time in his life when his father expected anything but the worst in him? If there had been such a mythical and happy time, Chuck sure as hell couldn't remember it. Perhaps before he was born Bart had hoped for a son as perfect as he was. But, then again, it had probably been easier for Bart to see the potential for goodness in his son if he hadn't killed his mother. Murderers, even of the infant variety, have a hard time garnering sympathy.

Since birth, it seemed as if nothing Chuck did was ever good enough for the great Bart Bass. And Bart never had the slightest problem making sure Chuck knew exactly how subpar he really was. If Chuck had managed to color in the lines, his father would criticize the amount of purple he'd used. If he built a Lego skyline full of tall skyscrapers, much like the ones his father built, Bart would point out each and every structural flaw. It wasn't enough to just be good, Chuck was supposed to be perfect. The more Bart demanded perfection from his son, the more Chuck grew to resent the man. Chuck's life became a constant cycle of rejection and feelings of inadequacy issued by and because of Bart. And no matter how deeply Chuck attempted to repress such feelings, he still felt the adolescent urge to please his stone-faced father.

So he continued to try. But because Bart Bass could rarely muster an emotion other than disapproval, Chuck continued to fail. No matter how strained the relationship with his father had become, the fallout always took him by surprise.

And that stung.

It was just another reminder, drawn from a very long list, of everything Chuck tried to forget. He would forever be too stupid, juvenile, arrogant, lazy, and all together inadequate in Bart's eyes. All over again, Chuck was faced with the lonely reality that he really was alone in the world. His father had died sixteen years ago, along with his mother, leaving their only son an orphan in everything but name. A filthy-fucking-rich orphan, but an orphan all the same.

Once upon a time, this had meant Chuck would spend the next few weeks mired in a deep cloud of self-loathing and doubt. But the benefit of being sixteen and loaded meant that any emotion could be easily buried under a binge of scotch, whores, and drugs. It all left him numb, which was exactly what Chuck preferred. It was a defense mechanism developed after years and years of emotional abuse. Emotions were a liability. And so Chuck withdrew from his father, his friends, and the world one toke at a time until a concrete wall separated Chuck from the world.

One of the few people to be allowed past that concrete barrier had been his best friend, Nathaniel Archibald. The more Chuck thought about it, the more he realized that their friendship had been doomed from the start. Despite living within blocks of each other, they lived in two truly different worlds. Nate was everything that Chuck was not. He was athletic and agile, quick to smile, and beamed with a halo of goodness and golden perfection. Nate had two parents who, despite their numerous flaws, loved him. But Chuck had never begrudged him any of that. He had outgrown flailing his arms helplessly at the many injustices of the world before he'd turned six. Even six year olds as stupid, lazy, and arrogant as Chuck Bass understood that life was never fair. And crying about the unfairness never changed anything.

But it remained that the two boys that had bonded during a business deal between their fathers had turned into two very different people with two very different outlooks on life. Everything Nate touched turned to golden perfection. Everything Chuck touched seemed to wither and die. Where Nate saw optimism, Chuck saw naivety. Nate trusted everyone. Chuck trusted no one. They were a real life version of Goofus and Galant.

The fight had never really been about Blair. Nate's feelings for girls ran about as deep as a puddle. He loved Blair today, Serena tomorrow, and Brooklyn next week. Nothing ever lasted because Nate was already on to the next bright and shiny object. But Blair had been the one girl Nate could hold over Chuck's head. She was the one girl that Chuck couldn't and wouldn't touch out of respect for Nate. And so Chuck stood by while Nate blundered through a relationship with Blair. Chuck had kept his mouth shut as Nate dated Blair while lusting after Serena. And despite the undeniable chemistry he felt with Blair, Chuck denied himself ever looking at Blair as anything other than an extension of his best friend.

But once that umbilical cord had been severed, everything had changed. At least for a few hours, Blair was no longer bound by her incessant need for a fairytale ending. She was wild, unpredictable, and incredibly… sexy. Even the great Chuck Bass could do little more than raise his eyebrows and glass to her in surprise. He all but waved a little white flag of surrender as the petite brunette entertained the entire room with her milk chocolate eyes and her gyrating hips.

In the limo, his words to her hadn't been an attempt to lure her into his bed. They had been words as open and honest as Chuck Bass got. And, in the end, she had made the first move. She crossed the boundary first. And Chuck had readily accepted what Blair had offered Nate time and time again. In so doing, Chuck somehow managed to do something the golden prince had never been able to do: make Blair happy. Not the kind of happy where her mouth didn't match her eyes. It wasn't even the fake happiness that Blair got from seeing her life go according to her mental script. It was a deep, glowing happiness. It was a giddy happiness, complete with a smile that went straight to her eyes, wrinkles be damned. Her covert relationship with Chuck, for all its fucked up qualities, made her happy. It made them both happy.

Despite being in a relationship with Blair for years, Nate had never made her smile like that. Hell, in all his years Nate himself had never smiled like that. At least not while sober. And Nate had certainly never expected his dark and dangerous friend, who had always made Nate look particularly golden, to find happiness as well. Not when Nate had searched so torturously for that very same happiness himself, without success. It wasn't fair. Blair was his, damn it. If she was going to be happy with anyone, it was going to be him. And, in return, she would bring him happiness as well. And Chuck would continue to brood and fuck anything with implants and a vagina. That's the way it was supposed to be. The truth was that, for the first time in his life, Nate was actually jealous of Chuck. And, for those reasons, Nate resented Chuck.

Chuck shrugged his shoulders at that thought as he lazily flicked the end of his joint into the street below. Nate had been his constant companion since they were boys. He would miss Nate.

But even Nate wasn't worth ruining his high, Chuck thought with a half smile as he lay back against the concrete.

Drugs… the perfect answer for teenage angst.


End file.
